


Sam Winchester and the Tentacles of Pleasure

by omgbubblesomg



Series: Team Free Will and the Tentacles of Pleasure [2]
Category: Supernatural
Genre: Accidental Voyeurism, Blow Jobs, Consentacles, Dicktacles, Episode: s13e17 The Thing, Hand Jobs, M/M, Multi, Other, Sounding, Tentacles, reluctant wincestiel
Language: English
Status: Completed
Published: 2019-11-23
Updated: 2019-11-23
Packaged: 2021-02-25 21:28:12
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 2,764
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21532234
Author URL: https://archiveofourown.org/users/omgbubblesomg/pseuds/omgbubblesomg
Summary: The baby tentacle monster looked like a handful of cooked noodles, and if anyone had bothered listening to Dean’s “Let’s just shoot it” suggestion then maybe they wouldn’t be in this mess, but apparently he was the only one with any common sense these days because now there was a lump of sentient spaghetti trying to hide in Sam’s esophagus.
Relationships: Castiel/Dean Winchester/Sam Winchester, Castiel/Dean Winchester/Sam Winchester/Tentacles
Series: Team Free Will and the Tentacles of Pleasure [2]
Series URL: https://archiveofourown.org/series/1551799
Comments: 78
Kudos: 137





	Sam Winchester and the Tentacles of Pleasure

**Author's Note:**

  * For [Paradigmenwechsel](https://archiveofourown.org/users/Paradigmenwechsel/gifts).
  * Inspired by [Dean Winchester and the Tentacles of Pleasure](https://archiveofourown.org/works/14491278) by [HazelDomain](https://archiveofourown.org/users/HazelDomain/pseuds/HazelDomain). 



> This fic is dedicated to all the very sexy and cool people who commented on the last installation. Most especially Paradigmenwechsel for being so thirsty for dicktacles.
> 
> Many thanks to Majesticduxk and Troubleseeker for jumping on board to beta at the last minute, and to the multishipper discord for letting me post tentacle lines all day as I wrote this.

The baby tentacle monster looked like a handful of cooked noodles, and if anyone had bothered listening to Dean’s “Let’s just shoot it” suggestion then maybe they wouldn’t be in this mess, but apparently he was the only one with any common sense these days because now there was a lump of spaghetti trying to hide in Sam’s esophagus.

“Hold still,” he ordered, putting fingers in Sam’s mouth to scoop out another tentacle. Sam wailed and flailed. He flwailed.

“It’s holding his uvula,” Cas observed. Dean peeked into Sam’s mouth and, yep, the thing had a stranglehold around the dangly bits at the back of Sam’s mouth. Sam made a gagging noise and tried grabbing at it, but it really wasn’t going anywhere.

“Want me to shoot you in the face?” Dean offered.

“UCK OO!” Sam yelled back, which was a bit rude. It wasn’t Dean’s fault there was a tentacle baby applying for a visa to Sam’s throat. Even if it _had_ been hatched in Dean’s belly like three minutes ago. Speaking of which, he really needed to find a new pair of pants.

Cas contemplated the situation for a moment. “We could try enticing it away? It seemed to enjoy pleasurable stimulation last time.”

Dean gestured at Sam’s noodle-covered face. “Be my guest, man.”

“I’m an angel, you can hardly expect me to—”

“Oh, what, so it’s better if I kiss my own brother?”

“That’s certainly more appealing than—”

“EEERGHHHEERRRGG!” Sam yelled, pointing at his face. He was turning a little bit blue. Which. Ugh. Fine. _Fine._

“Together?” Dean offered, and he leaned forward to peck Sam on the tiny bit of lip that wasn’t covered in tentacle. Cas did the same on the other side. The noodles didn’t let go, but they did stop squirming a little bit.

Cas put his hand on Sam’s chest and Dean watched as he leaned in a little more, tongue visible between the noodles because apparently being ententacled warranted French kissing. Dean sighed heavily and pointed a finger directly at Sam’s eye.

“You tell anyone about this and I’m switching your shampoo for Nair,” he promised. And then leaned in and kissed the side of Sam’s mouth, shutting his eyes so he could pretend he was sticking his tongue in a normal stranger from a bar who happened to have tentacles on their face, instead of his very un-normal little brother, who also happened to have tentacles on his face.

The tentacle creature puffed up a little bit in between their faces, and Sam gave a full body shudder which Dean graciously decided not to comment on. Then the creature seemed to deflate a little bit, and it dropped into Sam’s lap.

Sam shoved them both backwards immediately, wiping his face. “Ugh,” he said. “Ugh, ugh, no, ugh, please, oh god, yuck.” He spat out something thick and gooey, the origin of which Dean very carefully tried not to think about.

The tentacle lump in his lap flopped to the side. Sam looked down at it with the same expression he wore when Dean threw up the Seafood Special into his favourite pair of slippers.

“Grenade launcher?” Dean asked.

“Grenade launcher,” Sam agreed.

Cas nodded.

Dean nodded.

The creature nodded.

Oh wait, that wasn’t nodding. It was holding itself up on two trembly noodle-legs, bobbing gently, like it was looking around. Probably looking for a new hidey-hole. “We should put that in a Tupperware container,” Dean said, about three seconds too late.

It extended a long tentacle towards Sam’s midriff, and when Sam tried to swat it away it swatted him back, and then it launched itself at the waistband of his jeans, squeezing under his belt and into his pants before any of them could move.

“This isn’t going to end well,” Cas muttered, a millisecond before things started going not well.

Sam _screeched,_ and started writhing, clawing at his jeans.

“Get it out!” he shrieked. “Get it out! Get it out!”

_Please let it not be hiding in his butt, please let it not be hiding in his butt._

Cas ripped Sam’s jeans in two from the front to the back, so it looked like he was wearing a pair of very long footless jean socks. (Jootless Jocks?) And then shoved the pieces down to his thighs.

There was a tent in Sam’s underwear, and for possibly the only time in his life, Dean really hoped that what he was looking at was his brother’s boner.

But no luck.

The tent moved, wriggling from the front of Sam’s underwear to the back. Possibly sensing where this was going, Sam rolled onto his stomach and shoved his underwear down so he could put hands over his butt, trying to cover it.

“No, no, no, no no no,” he begged. Dean felt like saying the same thing about being forced to look at his brother’s ass. “Help!” Sam yelled at them.

“What is with this thing and butts?” he asked the room at large. Cas shrugged helplessly. Apparently they were both a bit leery of putting their hands anywhere near either Sam’s ass or the ass-obsessed ramen. But it didn’t seem to matter. Sam was doing a good enough job of protecting his virtue, or whatever. The creature probed his fingers but couldn’t find a way to slip past them. It slithered back under Sam’s belly.

“Well thank god for that,” Dean muttered. He started looking around for his own clothes. Half-naked-Sam was enough Winchester Nudity for this bathroom.

He was just about to grab a towel to wrap around his waist when Sam started screaming for _real_. He deliberated just leaving him to it. Surely his brotherly duties were over?

Sam screamed again and, dammit, dammit, god fucking dammit.

“What is it now?” he snapped, turning back around. And, oh. _Oh._ _That’s_ what.

Sam had rolled over onto his back, his underwear around his knees. He was staring down at his cock with the kind of expression you would use if a tentacle creature was slithering into your dick. Which, surprisingly, was exactly what was happening.

 _“NO!”_ Sam yelled, trying to grab a tentacle. But the thing had compacted into a thick, slippery rod, covered in little cilia. Sam’s hands slipped off it as it wormed deeper. His cock bulged around the intrusion.

 _Well,_ Dean thought. _I’ve lived a good life. Time to gouge out my own eyes and die from blood loss._

The bulge reached the base of Sam’s cock, and Sam’s eyes rolled into the back of his head. “No,” he wailed, “no, fuck, oh god, make it stop.”

His clutching hands tried to pinch at the last little bit of tentacle still poking out from the head of his dick, but it slithered out of his fingers and with an oozy sort of _squelch_ it disappeared down Sam’s slit.

If there were medals for _Not Throwing Up On Your Brother_ then Dean deserved gold. But it was a close fucking call.

Sam was writhing on the bathroom tiles, hands cupped around his junk. Dean tried to back towards the door, giving off _nothing to see here_ vibes with every inch of his being.

“Don’t you dare leave,” Sam wheezed. “Dean, don’t you, oh fuck, you gotta help.”

“Cas can help,” Dean pointed out hopefully. “Cas wants to help, see, look at him.” Cas looked like he had just eaten an entire bag of lemons.

“Please,” Sam wailed. “It’s, oh, oh Christ, it’s moving, I can feel it.”

Dean mentally awarded himself the most expensive bottle of alcohol he could get his hands on next time he went shopping. He stepped closer and knelt down at Sam’s side, and gingerly grabbed his wrists, trying to peel his hands away.

Okay, easy. This was easy. Piece of cake. He was being gentle. He was being normal. He was…

He was looking at his brother’s dick.

Objectively, he supposed it was a nice dick. Thick and long and, okay, maybe it looked a little bigger than his but that was just the lighting.

It was also ramrod straight and hard enough to pound a nail into bedrock.

Farther down, Sam’s balls were tucked up tight into his body, like there were looking for somewhere to hide, too. _You and me both,_ Dean thought.

And then, as he watched, Sam’s testicles began to… _swell._ The skin stretched out as the insides ballooned up.

“Oh dear,” Cas said calmly, earning himself a meeting with Dean’s best _Are you kidding me_ glare as soon as this was over.

Sam’s body clenched and he curled in on himself, whimpering. His nuts were still growing, swelling up as though something—and Dean had a good idea what that something might be—was filling them up from the inside.

“Anatomically,” Cas said, “that’s actually quite impressive.”

“Out,” was all Sam could reply; reduced, apparently, to one-word sentences. “Out.”

Cas looked at Dean. “Perhaps pleasure will entice it out again,” he said, like he was commenting on a weather report. A particularly tentacly, incesty weather report.

“I’m not here,” Dean muttered. He looked up at the ceiling. “I’m not here.”

Ha. Tough luck for all of them. His eyeballs especially. He was very much here.

Gingerly, he picked up Sam’s wrist, spat into his palm, and put Sam’s hand on his dick. “Go on,” he urged. “Entice away.”

Sam moaned and began to jerk off, his other hand cupping his balls. If anything, they only grew bigger.

Cas looked thoughtful. “Perhaps—” he said.

“Don’t say it.”

“Perhaps if we—”

“Cas, don’t say it.”

“Perhaps suction will help to expedite this process.”

“You said it.”

Sam’s hand was still moving on his dick, but there was no sign that the tentacle baby was interested in taking the opportunity to exit its new home. Sam was white as paper, panting into the ground in quick little breaths like he was doing his best to not move too much. Sure, Dean didn’t want to be here, but he also hated seeing Sammy hurting.

“I really am the best brother in the whole world,” he grumbled. And then he leaned forward, opened his mouth, and resolutely started reciting baseball stats as he got into place over Sam’s crotch.

 _It’s not so bad,_ he lied to himself. _That salty taste could be anything, really._

“You need to suck,” Cas told him, the unhelpful little shit.

Dean pulled off to say, “Why don’t _you_ suck?” So of course Cas got down onto his knees next to Dean, and put his mouth on Sam’s dick.

Dean was very, very concerned about his brother’s welfare, which is why he didn’t look away. And that’s how he ended up watching as Cas’s lips stretched out over the head of Sam’s cock, and then he also ended up watching the way Cas’s cheeks hollowed as he sucked, and he thought longingly about getting his own dick sucked.

 _What an interesting thing to think about your best friend and your brother,_ he thought, detaching himself completely from his own brain.

Sam’s hips lifted off the tiles. He made a high-pitched sound that Dean would have filed under the “desperate sex whine” category if it didn’t automatically get filed in the “noises that your brother makes and we never think about again” category.

“You’re doing great,” he went for instead, trying to inject a bit of serenity into his voice. “You’re doing so well, I’m so proud of you, you’re the— _JESUS FUCK WHAT THE FUCK.”_

So much for serenity. The base of Sam’s dick was bulging out, like Cas was sucking a ping pong ball through a straw instead of a tentacle through a dick-hole.

Cas fell back, gasping, and the bulge shrank downwards, no doubt disappearing back into Sam’s testicles.

“That was fucked up,” Dean told them both. “I am not okay with that.”

“Hurry,” Cas said, panting and gesturing at Sam’s crotch. “Keep sucking.”

 _Absolutely not,_ 99% of Dean’s brain went. But there was still 1% that wanted Sam to be tentacle-less, and the 1% was dumb as fuck.

He put the head of Sam’s cock back into his mouth, and sucked. _Hard._

 _This could be anyone’s dick_ he told himself. _I could be sucking anyone’s dick right now._

“Dean,” Sam moaned. “God, Dean, yes, harder.”

 _I could be sucking anyone who sounds like Sam,_ he amended.

Sam’s palms found the back of his head, holding tight. His stupid enormous hands almost encompassed his whole skull.

 _I could be sucking anyone who sounds and looks like Sam,_ he tried.

The base of Sam’s dick bulged again, as the tentacles returned. Dean sucked harder. Sam took one hand off the back of his head to fist himself roughly, fingers forming an O-shape that he thrust into sharply, his hand colliding with Dean’s nose on every pass.

The bulge crept incrementally upward, making it almost an inch before Dean’s jaw started to ache. He fell backwards. “Cas,” he gasped, but Cas was already in place, putting his mouth back over Sam’s dick so Dean only had to see the flushed wet head of it for half a second before it was covered again.

 _Flushed from me,_ he didn’t think.

 _Wet from my mouth,_ he also didn’t think.

Cas pulled the creature another half an inch before Dean took back over. Another half an inch. Another. They kept swapping back and forth while Sam made pornographic sounds beneath them and Dean ignored his own very hard cock and also the bulge in Cas’s suit pants. They were going to have to sign some kind of gentleman’s agreement after this, to never ever ever discuss what they had seen or heard in this bathroom.

Sam’s horrifically distended balls shrank as his horrifically distended cock grew. Dean had to put a knee on his chest to stop him from trying to push them off when the stretch got too much. There was only one way those tentacles were coming out, and he wasn’t willing to give up the head-start they’d earned.

“Dean,” Sam garbled, “Dean, please, please, oh, _oh._ That feels so good.”

“That’s Cas,” Dean pointed out, because it was Cas’s turn on the lollipop machine.

“Cas,” Sam rectified without opening his eyes. “That fucking, ow, ow, oh, it hurts, ah, fuck that feels good.”

Dean rolled his eyes and sucked Sam’s cock back in as Cas leaned back, massaging his jaw. “We’re almost there,” Cas noted. The bulge was right at the tip of Sam’s cock.

“Me, too,” Sam admitted, voice thin and reedy.

Dean winced and made a mental note to get out of the line of fire as soon as the tentacle baby was clear. That was not a trauma he needed to put himself or his future therapist through.

Cas propped a plastic container next to Dean’s chin, ready to catch whatever came out.

“Almost,” Sam groaned. “Almost, almost.” He was really working his cock now. Tight, fast strokes. His hips were making aborted little thrusts into Dean’s mouth even with both Dean’s and Cas’s hands trying to hold him down.

Cas leaned in close to peer at Sam’s dick where it disappeared past Dean’s stretched lips. “Get ready,” he said conversationally.

Sam lifted up off the tiles, his body going bowstring-tight. _“Gahh!”_ he wailed, fisting himself so fast his hand was almost a blur. Dean knew what it felt like to try and get your body over the line _now,_ but this almost looked too painful. He squared his shoulders and _sucked._

Sam arched even harder, yelling their names, and Something blurted onto Dean’s tongue. He pulled off immediately, and an explosion of tentacles and white— _not thinking about it_ —fluid spurted from the place where his mouth had been a moment before, landing with a _splat_ in the container.

Dean’s brain decided that this was one straw too many, and it departed his head, no doubt looking for greener pastures somewhere near his kidneys.

“You said our names while you achieved climax,” Cas said warmly, reaching out for Sam’s hand.

“Nnnh,” was all Sam could manage in response.

“That’s probably something we shouldn’t dwell on for too long,” Dean pointed out.

“Nnnh,” Sam agreed.

“Well what _am_ I supposed to be dwelling on, then?”

Dean sighed, and looked down at the plastic container. “Well,” he said. “We should probably start with the fact that you forgot to put the lid on.”

Sam and Cas looked down, too.

The container looked back at them, white gunk on the bottom and not a tentacle in sight.

“Oh no,” Cas said.

**Author's Note:**

>   
>   
>  (Fabulous additions by [TheLittleRedWhoCouldWrite](https://archiveofourown.org/users/TheLittleRedWhoCouldWrite))
> 
> For your regularly scheduled "Read More" I implore you to read the fic that started this all: HazelDomain's [Dean Winchester and the Tentacles of Pleasure](https://archiveofourown.org/works/14491278/chapters/33476460). I'm also reccing [You Never Expect To Have To Pee On Your Brother](https://archiveofourown.org/works/21349201) by Fledhyris! Dean and a giant jellyfish and one very reluctantly helpful brother 😂😂 And then instead of another fic rec why not go check out Trouble's [Sam/tentacle](https://twitter.com/_Troubleseeker/status/1179117544948539392) art, or Threshie's [Dean/tentacle](https://twitter.com/threshafterdark/status/1114018324252381186) art :D (BOTH LINKS ARE NSFW)
> 
> EDIT:  
> Trouble has informed me that because Cas is the only one who hasn't had a tentacle in him yet, we need to take a poll on how the creature will get inside.  
> For the record, the current tally stands at:  
> Nose: 1


End file.
